A First Love's Mistake
by LegendsNeverDie0103
Summary: Some say their first love is their kind kindergarten teacher. This situation is kinda like that. Except Ai's first love is her middle school chairman that enjoys instilling fear throughout the school. Of course, first loves don't always work out, and Asano Gakushuu will be sure to show her that. "You know, I'm a much better man than my father." "Please, you're delusional." ASANO/OC
1. Prologue: Stalking, But Not Exactly

**Disclaimer: I do not own anything from Assassination Classroom**

 **AUTHOR'S NOTE: Another odd Asano/OC pairing for you Asano fans! Please enjoy!**

* * *

 **"'Stalking' is such a strong word. I prefer 'intense research of an individual'."**

 **-Anonymous**

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 **PROLOGUE: STALKING BUT NOT EXACTLY**

She watched him. At assemblies, in the hallways, when he stepped into his car. She was always there, watching him intently as if the meaning of life was written across the man's forehead.

It wasn't unhealthy, no, of _course_ not! It was completely normal to have your attention caught automatically by the person you _respected._ Yes, respect. That was all it was. In no way, was she _stalking_ the man, not at all!

It was just mere _coincidence_ that she ran into him at the book store (the one he _coincidentally_ frequented) or the café (the one that was _coincidentally_ his favorite). It seemed that fate was just _adamant_ to have the two together.

Or at least that's what Tsukino Ai loved to think.

But seriously. Let's be honest here.

Since her first year at Kunugigaoka Middle School, she has been diligently gathering information on Asano. Yes, _that_ Asano.

Slyly slipping in a "Yeah, I saw him at that new restaurant the other day," when _he_ came up in a conversation with her friends and waiting eagerly for something along the lines of "Oh, I saw him at the bookstore by WcDonalds too yesterday," to be said. She would then take the newly learned info, store it in her mind, then allow it to become her " _new favorite bookstore."_

Oh, the lengths she would go to for the Board Chairman, Asano Gakuhou…

What? You thought Asano _Gakushuu_ was her crush? You must be joking. His father was so much smarter, so much more charismatic, and so much more talented.

Of course, she made sure to not get on his bad side since he was the son of the object of her affections.

Is she expecting to have her feelings reciprocated?

No, not at all.

Can she still admire him from afar?

Hell yes.

* * *

He watched her. When she was hiding behind buildings and signs with a dreamy gaze in her eyes. He was usually there, watching her intently as if she was the craziest person on the face of the Earth.

And she probably was.

Because who could ever have such a blatant crush on his demon of a father?

Besides his mother, of course, but he thinks that even she must have been under some kind of black magic spell or had a few screws loose when she agreed to marry that man.

Anyway, not the point. Enough about his mother and back to the topic at hand.

But yes, he did notice that foolish girl that seemed to follow his father around like a lost puppy.

He knew that the chairman was handsome; he received many of his features from him after all. It was inevitable that his father would have admirers, but none have ever acted upon it because of his untouchable demeanor. So to see a female, his age no less, be so bold as to be so obvious about her attraction towards the board chairman… was odd.

Stupid, but odd.

And it made him curious.

It wasn't _stalking._ He was merely observing her actions, trying to grasp what drew her to his father so much. This was perfectly normal and justified.

At least that's what Asano Gakushuu believed in his mind.

But again. Let us all be honest here.

He was interested. Not necessarily in her as a person. But in winning. He would prove that he was a much better person than his father. This was just an experiment.

Did he actually have _feelings_ for her?

Obviously not.

Would he still use her as just another way of besting his father?

Most definitely.

* * *

My, my, this was becoming interesting. Yes, he was fully aware of what was currently happening here. _He was the one who prompted it after all._ How, you ask? You'll find out very soon, I guarantee you.

Oh, how entertaining it was to watch those two play this childish game of cat and mouse.

That was the thought that ran through the mind of one Asano Gakuhou.

* * *

This was complicated and quite simple at the same time.

To be short about it, Tsukino Ai " _admired"_ Asano Gakuhou, Asano Gakushuuu " _observed_ " Tsukino Ai, and Asano Gakuhou simply gazed at them from above in amusement as he waited patiently for the show to begin.

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 **AUTHOR'S NOTE: How was it? If you liked it FOLLOW, FAVORITE, AND REVIEW!**


	2. Chapter 1: Challenge Accepted

**Disclaimer: I do not own anything from Assassination Classroom.**

 **AUTHOR'S NOTE: New chapter! Enjoy!**

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 **"I'm not playing 'hard-to-get'.**

 **I'm playing 'leave me the fuck alone'."**

 **-Anonymous**

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 **CHAPTER 1: CHALLENGE ACCEPTED**

"It seems that you have a little _stalker,_ Chairman." He had mocked him one day, just a small line he'd said to see if he could spike any reaction from the man though he knew it was highly unlikely Gakuhou would be taken aback by anything.

And he wasn't disappointed when his father showed no visible indication of being bothered. However, he _was_ surprised at his next words.

"Why, Asano-kun, are you jealous?"

The younger boy scoffed. "Why should I be?"

"Well, it can't be helped. Females tend to be attracted to those who wield the most power. It's no surprise that she would choose me before you." Asano could feel a vein that was threatening to pop out in his anger that was slowly building. Only his father could rile him up like this. But he wouldn't go down without a fight.

"Are you _enjoying_ the attention of a girl over _20 years_ your junior? I wasn't aware you were such a sick pervert."

"Ah, of course, I won't allow her to act on her desires, but it is quite flattering. And Asano-kun." The chairman leaned forward in his chair and linked his hands beneath his chin, the actions soon followed by a bright smile. "You'll never be able to control me if you can't even win the affections of some little girl."

Asano clenched his fists in rage and with a small but audible "Tch!", he exited the room.

Gakuhou was satisfied. He knew his son and he also knew that he would surely act upon the challenge. Gakushuu would 'succeed' in beating his father and be proud, only to become crestfallen when he learns that the second he had won that battle, he had ultimately lost the war. Everything would go according to Asano Gakuhou's plans, just as they always do. "The curtains have opened and now the show must begin."

He has to get his entertainment from _somewhere_ after all. Who better to play the clown than his very own son?

* * *

 **AI**

It wasn't like this in the beginning, really. It started out as an innocent admiration, then a budding fixation, and soon, a deep obsession. What was at first just glancing at him when he walked by turned to fervently seeking him out which soon rose to going out of her way and gathering information on him to learn his habits and preferences.

She'd tried to stop, but every time, she felt a yearning to see him again. It went to the point where she would base her actions on what he would believe was worthy. In her first year, she was in the D-Class, but after finding out that he liked people with power and intelligence, she had spent sleepless nights studying intensely and by her second year, she was miraculously bumped up into the A-Class, ranking 9th in the entire school. It was amazing what "love" could do.

Looking for Asano Gakuhou was routine to her now, something that's merged into her lifestyle. He was the only man that she felt attracted to…

And then _he_ had to come and ruin everything.

Damn that Asano Gakushuu to hell.

* * *

Today was a strange day. Normally, she would just sit down, read a book, and wait for class to start. However, before she could get seated, a voice called out to her. "Tsukino!" Asano- not the one she liked, unfortunately- approached her with a charming smile. "Why don't you sit with us today?" he asked as he gestured to himself and the other members of the Five Virtuosos.

Ai was confused. They had never talked before unless it was about simple class matters, but outside of that, nothing. They were just fellow classmates; nothing more and nothing less. Why was he trying to break that? There didn't seem to be any point.

"…Um… I'm not trying to be rude when I say this, but… why?"

He blinked for a second as if he had never expected her to even hesitate coming to spend time with him—which wouldn't be surprising considering the plentiful amount of girls that would have killed to be in her spot—but he quickly regained his composure and gave her another blinding smile. "I just wanted to be able to get to know you." He took a few strands of her hair into his hand and placed his lips against them gently. "You seem like such a lovely lady after all."

She stared blankly at him, not the smallest hint of a blush on her face. "Uh… thanks?"

Again, not the expected actions. He almost faltered once more, but just smiled, though this one seemed much more forced. "So would you like to sit with us?"

"…Sure. Why not?

* * *

The rest of the day dragged on in a similar fashion. He'd carried her books for her, helped her with difficult problems in class, and invited her to eat lunch with them. To be honest, he was starting to creep her out.

No one really knew _why_ he was doing this, not even the Five Virtuosos who were known to be his closest friends. Yes, she wasn't bad-looking and her grades were spectacular (as spectacular as they can get with the Five Virtuosos there anyway), but Asano wasn't really the dating type and even if he was, he wouldn't be the one to do the chasing; there was no need to. Girls flocked to him already without him doing so. However, they all figured there must be some amazing reason and logic behind his actions that explained everything and he just didn't find it the right time to tell them yet. Asano never did anything without a reason, without logic. And that thought appeased everyone.

But Ai would rather not be involved in anything with him because she knew from the fake smile on his lips to the slightly dark glint in his eyes that whatever he had in mind could not be good.

* * *

 **ASANO**

He had been considerate and allowed her a chance to sit with him and the four other most popular students in the entire school, and the only thing she could say was _'Why?'_ Hadn't she ever learned that if you are bestowed upon with a gift, you should accept it graciously, no questions asked?

 _Obviously not._

It seems that she didn't realize just how _fortunate_ she was to be receiving such attention from him. In his mind, people should only receive one chance and if they were too stupid to realize the opportunity that was presented in that chance then that's their fault. But then he had been even nicer to her and gave her a 'second chance', despite the fact that he didn't even believe in such a phrase, and she had the gall to say, _'…Sure. Why not?'_ like it was so troublesome and he had been _begging her to sit with him._

He was irritated. It had been a while since anyone but his father was able to make him feel this way.

Ah, yes. _His 'father'._

 _He_ was why Asano was doing this and this will be all worth it in the end when he finally wins Tsukino Ai's affections and as a result, wins against the chairman for once.

* * *

Ai had never realized that Asano had seen her when she watched his father because she had simply never felt his presence before. She may have always been too focused on the chairman to notice or maybe he was just extremely skilled. Either way was a possibility considering both their personalities.

But apparently he was there. (She never knew just _how_ many times he'd been there until much later on, but he'd hurriedly and hastily assured that, "the past was irrelevant".)

It came to her as a shock when he came up to her later in the day with words that made her blood run cold.

* * *

"I know that you're stalking my father." Ai froze. She glanced back and began walking forward again, much stiffer than before. "I'm talking to _you."_ She didn't respond and continued with her steps as she prayed that he thought he had gotten the wrong person. But alas, Asano Gakushuu was never wrong and everyone, including Asano himself apparently, knew that. "Tsukino Ai, I know that that's you. Now turn around!" he commanded. Ai paused, knowing that there was an extremely slim chance she would be able to escape. She could lie about her identity, but that wouldn't work for he saw her every day in class and had been pretty much stuck to her side the entire time today. She could run —she was literally right in front of the gates of the school, but she knew that his brilliant mind wasn't the only thing he was gifted with; he would catch her before she could take three steps. Ai slowly turned around to face him, looking right, then left, and then back at him, hesitantly pointing a finger at herself in question. "Yes, you, now stop acting stupid though I know it may be too much to ask."

She had only given him indifferent responses the entire day and now she had dared to try to avoid him. He was done with the nice-guy act.

She felt offense from the statement and it showed in her expression, but it was ignored.

"Um," she spoke up. Her voice was soft and hesitant. "Did you need something, Asano-kun?"

He remembered his purpose and nodded curtly. "Yes, I've wanted to discuss the topic of you following my father."

A tint of pink fell over her cheeks. "I-I don't know what you're talking about," she answered weakly. Asano rolled his eyes.

"Please, you don't need to hide it. You make it fairly obvious."

Her blush darkened into a deep scarlet as she whispered, "I do…?" in horror. He ignored her and continued.

"What I wonder though is why exactly you're so infatuated with that man. Is it his looks, his money, or authority? Or perhaps it's-"

"No!" she shouted, startling him. "It's not that. I just… I just admire his strength. Chairman Asano is smart and powerful and he doesn't let anything get in the way of what he believes in. I respect him for that."

"…Is that all?"

"Wha-?"

He stepped forward and she took one back only for her back to be met with the wall of the front gates. He placed his hands on either side of her head, his arms caging her in. His lavender orbs seemed to pierce through her with its intensity.

Now close to her, Asano gave the girl a once-over, actually looking at her for the first time that day. Blonde locks that waved slightly at the ends and wide emerald eyes—both of which that indicated she most likely had foreign blood running through her veins. She wasn't ugly, but he'd seen better and quite honestly in his opinion, probably deserved better. But if it's to beat his father, he really had no choice.

"If intelligence and power is all you desire then wouldn't I be a candidate that was just as well?" Asano began to lean forward and when their lips were mere centimeters away from each other, Ai panicked and did something that she sorely regretted seconds later.

She slapped him. Hard.

His head snapped to the side and there was only silence. "I…"

Slowly, his head turned back almost mechanically to face her and Ai could already see the bright red, hand-shaped bruise starting to form on his right cheek. But that wasn't what she was focusing on. A smile had stretched across his lips, but in no way was it comforting. Quite frankly, it was the most horrifying sight she had ever seen in all her 14 years of living and it would probably continue to haunt her dreams for the rest of her life also. Despite the warm, close-eyed smile he gave her, a terrifyingly, dark aura was beginning to manifest behind him. She had no idea how she could see such a thing, but she knew for a fact that it was there.

 ** _"You've got some nerve."_** The blonde-haired girl wanted to let out a scream of horror at his venom-laced words, but found that she couldn't speak. As if there were some invisible force stopping her from doing so. He leaned forward once more, this time to whisper threateningly into her ear. _"You'll regret this."_ Oh yeah, she knew she would. He didn't need to remind her. _"You know what's going to happen?"_ Ai squeezed her eyes shut as she waited to hear her death sentence. **_"I'll make you fall for me so hard, and then… I'll break you."_**

Uh… wait, what? He was gonna what now?

Asano straightened, took a few steps back, and then left.

She blinked. "What… the hell?"

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 **AUTHOR'S NOTE: Yeah, I know. The ending was pretty abrupt, but I thought it was a good place to stop. If you liked this chapter, FOLLOW, FAVORITE, and REVIEW please!**


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